As evaluation becomes more widespread and institutionalized, both the pros and cons of evaluation become more visible. This chapter discusses the theoretical possibility of a “skeptical turn” in evaluation, recognizing that the high hopes which characterized the early years of evaluation can no longer be the basis for the evaluation enterprise. The chapter argues that the following problems remain fundamental to evaluation: 1. Attention is a scarce resource in organizations, so more evaluation is not followed by more attention to evaluation. 2. The use problem in evaluation remains unresolved. This problem includes lack of use, unintended use, and constitutive effects of evaluation. 3. Evaluation does not always enhance accountability, but unfolds in complex organizational networks where accountability sometimes evaporates. 4. Evaluation sometimes becomes a victim of its own search for epistemological certainty, producing multiple forms of evaluative data and meta-evaluations. 5. Evaluation is too often used as a panacea. 6. Evaluation is costly in both visible and invisible ways. The chapter discusses whether a recognition of a “skeptical turn” in evaluation might be a fruitful way of enhancing self-reflexivity regarding evaluation and its use in contemporary society.